Perivine






Names

    • Q-100336
    • Perivine
    • PERIVINE [MI]
    • CHEMBL521377
    • HY-N6062
    • DA-56705
    • Vobassan-17-oic acid, 4-demethyl-3-oxo-, methyl ester
    • BDBM50480291
    • 2,6-Methano-1H-azecino[5,4-b]indole-14-carboxylic acid, 5-ethylidene-2,3,4,5,6,7,8,9-octahydro-8-oxo-, methyl ester
    • AKOS040758483
    • 2,6-METHANO-1H-AZECINO(5,4-B)INDOLE-14-CARBOXYLIC ACID, 5-ETHYLIDENE-2,3,4,5,6,7,8,9-OCTAHYDRO-8-OXO-, METHYL ESTER
    • 4-Demethyl-3-oxovobasan-17-oic acid methyl ester
    • 4-25-00-01712 (Beilstein Handbook Reference)
    • Perivin
    • Vobasan-17-oic acid,4-demethyl-3-oxo-,methyl ester
    • methyl (1S,14R,15E,18S)-15-ethylidene-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate
    • G388O8884F
    • UNII-G388O8884F
    • Vobasan-17-oic acid, 4-demethyl-3-oxo-, methyl ester
    • Methyl (1S,14R,15E,18R)-15-ethylidene-12-oxo-10,17-diazatetracyclo[12.3.1.0,.0,]octadeca-3(11),4,6,8-tetraene-18-carboxylic acid
    • Q27278686
    • BRN 0046952
    • 2673-40-7
    • methyl (1S,14R,15E,18S)-15-ethylidene-12-oxo-10,17-diazatetracyclo(12.3.1.03,11.04,9)octadeca-3(11),4,6,8-tetraene-18-carboxylate
    • DTXSID701043270
    • Methyl (1S,14R,15E,18R)-15-ethylidene-12-oxo-10,17-diazatetracyclo(12.3.1.0,.0,)octadeca-3(11),4,6,8-tetraene-18-carboxylic acid
    • CS-0032274

Attributes

  • Canonical SMILES

    C/C=C\1/CN[C@H]2CC3=C(C(=O)C[C@@H]1[C@@H]2C(=O)OC)NC4=CC=CC=C34

  • InChI

    InChI=1S/C20H22N2O3/c1-3-11-10-21-16-8-14-12-6-4-5-7-15(12)22-19(14)17(23)9-13(11)18(16)20(24)25-2/h3-7,13,16,18,21-22H,8-10H2,1-2H3/b11-3-/t13-,16-,18-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.19
  • #RotBonds: 1
  • MW: 338.407
  • HBD: 2
  • HBA: 4
  • logP: 2.6203000000000003
  • Chemical Formula: C20H22N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. holstii Kenya - -
    T. johnstonii Kenya - -

External Databases


References

  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Characterization of a Suspension Culture of Tabernaemontana elegans on Growth, Nutrient Uptake, and Accumulation of Indole Alkaloids*. Planta Med, 1989 (PMID 17262332).
  • Dichomine, a novel type of iboga alkaloid*,**. Planta Med, 1983 (PMID 17405059).
  • Plant anticancer agents III: Isolation of indole and bisindole alkaloids from Tabernaemontana holstii roots. J Pharm Sci, 1977 (PMID 561182).
  • Plant anticancer agents V: new bisindole alkaloids from Tabernaemontana johnstonii stem bark. J Pharm Sci, 1978 (PMID 621649).
  • Tertiary indole alkaloids from leaves of Tabernaemontana dichotoma. Planta Med, 1983 (PMID 17404903).

Compound-Protein Relationships


Compound Activities

    • Anticancer
    • Reproducible
    • Inhibitory
    • Antileukemic
    • Cytotoxicity

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -4.93
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.14
    Distribution Blood-Brain Barrier (Central Nervous System) -2.04
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.07
    Plasma Protein Binding 63.62
    Steady State Volume of Distribution 2.93
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 13.46
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor 0.48
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.88
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.89
    Micronucleos Toxic
    NR-AhR Toxic
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -2.29
    Rat (Acute) 2.96
    Rat (Chronic Oral) 2.07
    Fathead Minnow 4.37
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 435.77
    Hydration Free Energy -8.1
    Log(D) at pH=7.4 2.4
    Log(P) 2.12
    Log S -3.8
    Log(Vapor Pressure) -8.78
    Melting Point 246.24
    pKa Acid 9.46
    pKa Basic 5.19